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Novel glycosyl donor and thioglycoside compound, and preparation methods of thioglycoside compound

A compound and glycosyl technology, applied in the field of glucosinolate compounds and their preparation, new glycosyl donors, can solve problems such as limited application, difficult peptide and protein modification, complex preparation methods, etc.

Inactive Publication Date: 2021-01-29
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the application of the above method is limited by the configuration of the anomeric carbon thiol, which is only suitable for thermodynamically stable configurations, and requires multi-step synthesis, and the preparation method is complicated.
The study found that the reaction of organolithium reagent and Grignard reagent as sugar group donor and thioelectrophile can obtain two configurations (α, β) of the product, but it can only be reacted with 2-deoxysugar , and the compatibility of functional groups is very poor, it is difficult to apply to the modification of peptides and proteins, which greatly limits the application

Method used

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  • Novel glycosyl donor and thioglycoside compound, and preparation methods of thioglycoside compound
  • Novel glycosyl donor and thioglycoside compound, and preparation methods of thioglycoside compound
  • Novel glycosyl donor and thioglycoside compound, and preparation methods of thioglycoside compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] The synthesis of embodiment 1, compound 3, compound 3-x

[0074] 1. According to the following synthetic route, compound 3 is obtained:

[0075]

[0076] Step a: at room temperature, in the dichloromethane solution (wherein the concentration of 3-a is 0.5mol / L) of sugar 3-a (1eqiuv) of all hydroxyl groups, add acetic anhydride (addition amount is the number of hydroxyl groups on 3-a 1.2eqiuv), triethylamine (3eqiuv) and DMAP (0.2eqiuv), stirred overnight at room temperature. After the reaction, the reaction system was washed with saturated potassium carbonate solution, extracted with dichloromethane, dried over anhydrous sodium sulfate, filtered with suction, concentrated, and separated by column chromatography (300 mesh-400 mesh silica gel) to obtain the corresponding all-acetyl-protected product 3-b.

[0077] Step b: Dissolve the fully acetyl-protected product 3-b in acetonitrile (the concentration of 3-b is 0.5mol / L) at room temperature, add thiourea (1.5eqiuv) ...

Embodiment 2

[0085] Embodiment 2, the synthesis of compound 1

[0086]

[0087] 1-Allylsulfone-2,3,4,6-tetraacetyl-α-D-glucopyranose (Yield=75%)

[0088] 1H NMR (400MHz, Chloroform-d) δ5.99–5.79(m,1H),5.58–5.47(m,3H),5.31(t,J=9.3Hz,1H),5.10(t,J=9.8Hz, 1H), 4.56(d, J=9.9Hz, 1H), 4.34–4.16(m, 2H), 3.98(dd, J=13.9, 8.4Hz, 1H), 3.83–3.73(m, 2H), 2.10(s ,3H),2.05(s,3H),2.05(s,3H),2.03(s,3H).

Embodiment 3

[0089] The synthesis of embodiment 3, compound 2

[0090]

[0091] 1-(2-Phenyl-2-propenyl)-sulfone-2,3,4,6-tetraacetyl-α-D-glucopyranose (Yield=71%)

[0092] 1 H NMR (400MHz, Chloroform-d) δ7.50–7.46(m,2H),7.43–7.36(m,3H),5.77(s,1H),5.60(s,1H),5.50(t,J=9.6 Hz, 1H), 5.16(t, J=9.3Hz, 1H), 5.03(t, J=9.8Hz, 1H), 4.51(d, J=14.2Hz, 1H), 4.17(d, J=9.9Hz, 1H), 4.10–4.03(m, 3H), 3.29(dt, J=10.1, 3.5Hz, 1H), 2.10(s, 3H), 2.02(s, 3H), 2.01(s, 3H), 2.00(s ,3H).

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Abstract

The invention provides a glycosyl donor shown as a formula I and a preparation method thereof, and further provides a thioglycoside compound shown as a formula III and a preparation method thereof. The glycosyl donor provided by the invention is novel in structure and simple in preparation method. With the glucosyl donor as a raw material, the thioglycoside compound with a special alpha configuration is prepared by utilizing a photocatalytic free radical reaction, and the preparation method is simple, mild in reaction conditions and high in yield, and has very good application prospects.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a novel glycosyl donor, a glucosinolate compound and a preparation method thereof. Background technique [0002] Saccharides play an important role in many life activities and are important skeletons of many drugs and functional materials. Thioglycosides play an important role in the synthesis of sugar compounds and the modification of natural products. Many biologically active thioacetals are thioglycosides. Thioglycosides are used as glycosyl donors in many important glycosylation reactions. Thioglycosides are also very important glycosides. Compared with natural oxoglycosides, they have better hydrolytic stability while maintaining a similar three-dimensional conformation. It was found that, in addition to thioglycosides found in natural peptide chains, synthetically modified sulfur-linked glycopeptides are also highly resistant to chemical and enzymatic degrada...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/14C07H1/00C07H17/04C07H15/26C07H13/04C07H15/203C07H17/02C07D309/10C07D307/20C07D405/12C07K5/062C07K5/065C07K5/078
CPCC07H1/00C07H15/14C07H13/04C07H17/02C07K5/06052C07K5/0606C07K5/06078C07K5/06156C07H15/26C07H17/04C07H15/203C07D307/20C07D309/10C07D405/12C07D405/14C07D309/08C07D493/10C07D407/12C07D493/06C07D307/18Y02P20/55C07B2200/07
Inventor 钮大文张霞万立强曹金戈
Owner SICHUAN UNIV
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